All Photos(1)
Synonym(s):
Photochromic Ion Channel Blocker, QAQ, 2,2′-((diazene-1,2-diylbis(4,1-phenylene))bis(azanediyl))bis(N,N,N-triethyl-2-oxoethanaminium) formate, Quaternary Ammonium–Azobenzene–Quaternary Ammonium
Empirical Formula (Hill Notation):
C30H46N6O6
Recommended Products
Assay
≥95% (HPLC)
Quality Level
form
solid
manufacturer/tradename
Calbiochem®
storage condition
OK to freeze
protect from light
color
brown
solubility
DMSO: 25 mg/mL
shipped in
wet ice
storage temp.
2-8°C
General description
A membrane-impermeant Na+, K+, and Ca2+ channel blocker that is structurally composed of two azo-linked QX-314 (Cat. No. 552233) type quaternary amines. Both QX-314 and QAQ are shown to selectively target excitability of nociceptor neurons via TRPV1-dependent cellular uptake upon TRPV1 activation by Capsaicin (Cat. No. 211275). Unlike QX-314, the channel blocking potency of QAQ can be quickly switched off by an optical trans to cis isomerization upon 320 nm illumination, which in turn can be reversed back to the active trans configuration via 500 nm illumination. Its in vivo efficacy as a pain-selective, photochromic anesthetic has been demonstrated in modulating rat cornea tolerance to mechanical pressure (200 nmol QAQ/100 pmol Capsaicin/10 µl/eye). QAQ cellular uptake can also be achieved by ATP-activated P2X7 receptor, but not activated TRPA1 or TRPM8. In addition, QAQ is reported not to affect Kir (inward-rectifier) or HCN (hyperpolarization-activated cyclic nucleotide-gated) channels.
A membrane-impermeant Na+, K+, and Ca2+ channel blocker that is structurally composed of two azo-linked QX-314 (Cat. No. 552234) type quaternary amines. Both QX-314 and QAQ are shown to selectively target excitability of nociceptor neurons via TRPV1-dependent cellular uptake. Unlike QX-314, the channel blocking activity of QAQ can be quickly switched on and off via optical cis-to-trans (500 nm) and trans-to-cis (320 nm) isomerization. Its efficacy as a pain-selective, photochromic anesthetic has been demonstrated in rats in vivo. QAQ cellular uptake can also be achieved by ATP-activated P2X7 receptor.
Biochem/physiol Actions
Cell permeable: no
Primary Target
Ion Channels
Ion Channels
Reversible: yes
Packaging
Packaged under inert gas
Warning
Toxicity: Standard Handling (A)
Reconstitution
Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.
Other Notes
Mourot, A., et al. 2012. Nat Methods.9, 396.
Banghart, M., et al. 2009. Angew Chem Int Ed Engl.48, 9097.
Banghart, M., et al. 2009. Angew Chem Int Ed Engl.48, 9097.
Legal Information
CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Certificates of Analysis (COA)
Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.
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